Wheels, Heels and Demon Girls
by Slice'o'Pie
Summary: Sam's relations with demons caused Dean to nearly disown him. But what will Dean do now that he's got a demon lover of his own? (Serious Mature Story Fun Shenanigans and References)


**A Note: Just a heads up here, I plan for this story to be serious, but understand there will be lots upon lots of shenanigans and references to other media because I can't help myself. If you like what you read, tell me! I'll write more :)**

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"Well, I'll tell you what," the ferryman went on as he navigated the small motorized boat towards the dock. "You boys are just crazy now for coming out here all by your lonesome. Just crazy."

"So we've been told," Sam Winchester said, smiling politely at the ferryman, though he pressed his hands a little tighter together. Next to him, Dean wiggled in his seat, adjusting his collar.

"You think you might hurry this up?" He asked. "We're kinda' on a bit of a time crunch."

The ferryman merely chuckled to himself, but the boat continued on at the same speed. "Well, come morning time, maybe ya'll could convince the lady I dropped off here the other night to ride'on off the island with ya. If she's still there-..."

Dean and Sam exchanged a look. "What lady?" Sam asked.

"Oh, I can't remember her name. 'Nanny', something or other. Here to help find a missing friend, or somethin'. She was determined. Naive, but determined."

"Hold on," Dean's voice was sharp. "You told us earlier you didn't bring anybody else here-"

"No," the ferryman corrected. "I told you nobody else was on the island. I brought somebody over... don't mean she's still there. Anywho, here we are." The ferryman navigated the boat to the old dock, and he reached out, grabbing onto the wood to the hold the boat in place while Dean collected his backpack and Sam stood up to exit the boat first.

"Ya'll be careful now," the ferryman warned as he began away. "And whatever you do, don't recite Charlotte's poem!"

"Poem?" Dean wondered out loud to his brother as they stood side-by-side, watching the boat navigate away.

"Yeah, it was kind of like Bloody Mary- a game children would play. Children of the Thorton family and visitors would recite this poem in order to summon Charlotte to stir up the family gatherings."

"Huh," Dean spoke, already losing interest, and he let out a sigh as he readjusted the bag over his shoulder. "Well let's go. We don't have much time left before-"

"Hello?" A voiced called on the other side of the gates. Dean and Sam froze, listening as gentle footsteps approached the gate. "Hello?" the voice asked again.

The brothers sprang into action quickly: shotgun clenched in Dean's hands while Sam wasted no time in snagging his knife from his belt, the brothers cautiously crept towards the gate, squinting past the fog as they listened to the voice draw nearer and nearer. As they neared the black iron of the gate, just barely the fog began to thin, and as the gate let off a noisy whine when Dean eased it open with his boot did the figure of a woman emerge. Weapons raised the bothers inched forward, forward, forward, until...

"Hi! I'm Nancy Drew."

At the sight of the young blond the Winchesters immediately lowered their weapons. Sam's brows furrowed while Dean anticipated a very frightful -and very loud - reaction, his body tensing, but the blond, Nancy Drew, merely remained smiling up at them, blinking. Wearily Dean slowly looked to his brother,who met his gaze for just a moment before clearing his throat.

"Okay. I'm Sam, and this is my brother, De-"

"Are you both members of the Thornton family? You know the wedding isn't until next week, right?"

"Uh, no, we're not," Sam responded.

Nancy stepped forward. "Then what are you doing on the island then?" Her eyes narrowed suspiciously as she moved closer to the brothers, who instinctively leaned away in unison.

"Jesus, we don't have time for this. Look, lady, we're hunters, okay? And you're-"

An exaggerated gasp stole Nancy's breath as she hopped back, placing her hand on her chest. "Hunters?" She repeated. "That's terrible. And what right do you have hunting animals on somebody else's property? Just because they're not here doesn't mean it's right."

For the very life of him, Dean just couldn't wrap his head around this girl. For a slow second all he could do was merely stare into her blank, angry and naive eyes before finally he shook his head, and began to move past Nancy and past the opened gate.

"Hey!" She bellowed as Dean stormed passed, but Sam speaking back up stole Nancy's attention.

"Nancy, look, this is important. Why are _you_ here?"

"Well, I was invited here to look for my friend, Jessalyn. She's getting married next week, but she went missing."

"Missing? When did she go missing?" Sam asked.

"About a day ago," Nancy responded. "But Detective Drew is on the case!"

Dean let out a chuckle from behind them. " _You're_ a detective?" He asked, turning in Sam and Nancy's direction as he slung his shotgun over his shoulder.

"I sure am! Youngest sleuth to come from River Heights!"

Dean's brows furrowed as he glared. "Sleuth?" He repeated, quivering slightly. Now, Sam grew frustrated.

"Nancy, look, your friend is in some serious danger. I need to know everything that you know about this island, this family, and this ghost."

Nancy let out a laugh herself. "Boys, don't worry," she assured. "It's just a typical kidnapping. There's no such thing as-"

"Lady," Dean growled, moving towards them. "Your friend? _Jessalyn_? She's probably _dead_ by now."

"No," Nancy shook her head, still smiling. "She wouldn't be, doesn't fit a kidnapper's typical process. I have yet to find the ransom note, but I suspect it was Jessalyn's fiancé-"

"Yeah well, _ghosts_ don't have a process. They don't leave ransom notes, they don't give you a shot, they just _kill_. Charlotte is out for blood, and you're wasting our time. Sam, let's go!"

Dean turned and began down the wide path towards the Thornton mansion, Sam following hot on his heels, but behind them the blond began to wine.

"Hey!" She called, jogging up behind them, the fallen leaves crunching beneath her heels. "This is _my_ case, and _I_ intend to solve it." She quickened her pace to keep up with the brother's as they continued towards the front doors of the mansion.

"Nancy, look, there _is_ no case. It's pretty obvious what's happening around here." Sam stopped with Nancy at the front doors of the house, but Dean wasted no time with carefully opening the door before barging right inside while removing the EMF reader from his coat pocket. "Have you seen Charlotte?"

Nancy hesitated, before finally letting out a breath as she lowered her head. "Yes. A few times, actually. It was really scary! But... I'm just not sure I'm convinced."

Sam was trying, trying so very hard to get through to this lady, or at least _try_ to understand, but the longer he remained standing there, the more it felt like he was talking to a wall. Meanwhile, his brother was alone in the otherwise silent house, and Sam knew he couldn't waste anymore time. He gave Nancy an awkward smile before heading into the house himself without saying a word. Nancy, of course, was right behind.

"You know, I've already combed this place up and down for clues," Nancy pointed out with frustration, after having followed the brothers around for what seemed like ages. Now, the party was upstairs; Sam studying the multiple old paintings that hung on the walls in the great hall, Dean poking and prodding at objects with the barrel of his gun as he moved about the space with the EMF reader, while Nancy stood with her hip jutted in the middle of the room.

"Still not getting much of anything," Dean reported, looking down to the nearly silent EMF reader. "What's with the sleeping bag?" Dean asked as he circled around Nancy, his eyes falling back to the sleeping bag and lantern that lay on the floor in the middle of the room.

"It's mine," Nancy explained. "I was invited here?" She glared at Dean, who had ceased walking and stared back, coldly. "To find my friend? To solve the _mystery_?"

"There _is no_ mystery!" Dean growled, only for his attention to be stolen by his brother saying his name. With a final glare at Nancy, Dean moved around her to step by Sam, who remained studying a painting.

"Check it out," Sam said in a hushed tone, raising his hand to point at a section of the painting. "This part of the painting had been covered up, but someone scratched it off."

"Yeah, and I bet I know _who_ ," Dean turned his head slightly to glare at Nancy.

"Who is that?" Sam wondered, staring at the portion that had been covered up, a rather angry looking woman standing next to an unmarked tombstone in the Thornton family cemetery.

"That's Clara, Jessalyn's mother. In case you wanted to know," Nancy tossed, slipping her hair over her shoulder before crossing her arms and looking away.

"What's back there?" Dean wondered now, gesturing down a long hallway at a closed, white door at the end, his eyes falling to the EMF reader, which was starting to pick up some noise. Sam moved away from the painting to look down the hall as well. Just as Nancy began to explain, the brothers were already heading for the door.

"That's Charlotte's room," Nancy sighed, following the brothers quickly before she slowed her pace, growing a bit more hesitant once they reached the door. Dean slowly looked to her while Sam tried the door, only to find it was locked.

"And you haven't been in here yet?" Dean brows furrowed as he glared back at the blonde.

"The door is locked. I've been on the look out for the key," Nancy explained with determination, but Dean merely rolled his eyes as he turned back to the door, cursing under his breath. A gasp escaped Nancy as Dean kicked down the door, the boom echoing through the hall like thunder, and Nancy stood with her hands over her mouth as the brothers entered the room, weapons raised with caution.

The room wasn't terribly large. It was cold, the air stale, and the vintage style wallpaper had started to fade and rip, and hang from the walls. A large fireplace sat against the middle of the wall, its mantle lined with multiple analog clocks of different styles, each ticking noisily. On the wall adjacent, wide and tall paintings hung, portraying members of the family.

As the the EMF reader whined lightly, Nancy snooped along with the brothers, noisily peering over their shoulders to see what they were looking at before she scurried to the desk before Sam could reach it. _"Hmph!_ " Her shoulder's bounced as she picked up a small jewelry box, turning up her nose in pride. Sam's lips thinned as he bounced on his heel, his fingers curling to fists, but after a couple of deep breaths he manged to calm himself down.

No longer than perhaps a minute had gone past, but Sam was rapidly losing all patience. "Find anything?" He asked Nancy, his tone sharp.

"Not yet," Nancy said. "There's a puzzle on this box... Once we solve it, then- _Hey!"_

All patience lost, Sam reached around Nancy to grab the box from her hands. He set it down on the desk, pulled out his knife, eased the tip underneath the lid of the locked box, and pushed upward, causing the box to spring open.

"Must you be so obnoxious!" Nancy called, barging her way in between Sam, cutting off his access to the box, or ability to even see what was inside.

" _I'm_ the obnoxious one?" Sam muttered to himself, rolling his eyes as he listened to Nancy dig around nosily in the jewelry box, Dean chuckling lightly somewhere near the fireplace.

"Well," Sam said now, past gritted teeth. "What you got?"

"Just an invitation to Charlotte's party... an old chocolate kiss candy... and a-ha! A _key!_ "

Sam leaned forward in attempt to glance over Nancy's shoulder, but his impatience got the best of him. He snatched the key out of Nancy's hand and ignored her pouty protest as he turned around, examining the key. "Hey Dean, check it out." Sam glanced up as Dean stepped over to him. Meanwhile, Nancy had given up he attempts in getting the key back and her arms fell to her sides in defeat.

Once Dean reached Sam, the EMF reader began to whine noisily, the needle bouncing widely once he lifted it to point it directly at the key. The brother's exchanged a look before Dean placed the EMF into his pocket, and he reached out to rub his fingers over the key before examining them.

"Ectoplasm," he confirmed, holding up his hand for Sam to see. Sam let out a sigh as he shook his head slightly, and Dean looked back down to his thumb and index. "Man, I knew we were dealing with an angry ghost, but not this angry."

"We gotta hurry, Dean," Sam said. "Assuming any one of those clocks over there are correct, we only have about an hour left, before-"

There was no need for Sam to finish, Dean nodded, understanding exactly what Sam meant. "We need to find what that key goes to, figure out what's keeping Miss 'Up-In-Flames' here, and-"

"If that key has anything to do with this, and I'll bet it does, perhaps we should pay a visit to the crypt in the family cemetery!" Nancy interrupted behind them, her attention focused downward as something crinkled within her fingers. Sam glanced over his shoulder at her.

"You need to show us exactly whe-"

"Hold up," Dean's tone was sharp as he raised up his hand, glaring at Nancy as her jaw moved around in a chewing motion. "Did you just eat that old piece of chocolate that was in that box?"

Nancy continued to chew noisily. "Uh-huh," she nodded her head. Sam's brows met as he turned back to Dean, his nose crinkled. Meanwhile, Dean could not stop glaring.

"Really?" He barked, his jaw hanging slack. "Why? Just, wh- You know what? Nevermind. Sammy, let's go."

In unison the brothers began out of the room, and it wasn't long before they listened to desperate footsteps clinking after them.

The cemetery wasn't far from the Thornton mansion, and fortunately as they maneuvered their way around the graves, the brother's were able to talk quietly amongst themselves with no interruption from Nancy. They key did unlock the crypt, but unfortunately there was nothing of relevance within the concrete walls. Sam and Dean turned from that dead end, and were forced to follow Nancy's lead as she led them to the guest-house where Charlotte had died. The two story, smaller house was torched to a crisp; the roof was caved, walls of the house were broken and missing, and the surrounding forests around were bare, with nothing other than burnt stumps surrounding the area. Within Dean's pocket, the EMF reader whined obnoxiously as they explored the area.

"...I'm just saying accidental deaths don't lead to angry spirits. It doesn't add up," Sam was arguing his point with Nancy.

"There's no such thing as ghosts," Nancy fired back. "Ghost stories are just the excuse the bad guy uses. Jessalyn's fiance' said-"

"Guys," Dean barked, halting in his tracks, and once Nancy and Sam ceased arguing, Dean listened closely. The wind howled lightly as it traveled through the holes in the walls, but past Nancy's sighs of frustration, Dean could make out something coming, and it was angry.

"Sammy look out!" A round from Dean's shotgun echoed within the night as he fired at Charlotte, but the spirit disappeared too quickly for the bullet to hit. A scream erupted past Nancy as she fell to her knees, clenched in terror. This scream was easily ignored by the brothers, as it had been anticipated, however when Nancy began howling above the sound of her body dragging against the gravel, Sam called Dean's name, and his eyes fell upon Charlotte, pulling Nancy back towards the ruins of the guest house by her wrist.

"Help! Help! _Heeeeelp!_ "

Another round fired into the night, but once again Charlotte disappeared before the bullet could hit. Sam ran up to Nancy, helping to pull her to her feet. She groaned in pain as she she held her wrist, hissing again as the pain doubled at the touch. She pulled up her sleeve, gasping as the sight of fresh and hot burns to her skin, each in the shape of a finger.

"We need to find what's keeping her tied to this island and destroy it now," Dean barked, leaving Nancy no time before he immediately turned to head back to the house, Sam struggling to keep up as he helped Nancy along.

Within minutes Charlotte's bedroom was torn. Objects big and small had been tossed around as the brothers desperately searched for anything of sheer importance.

"Nancy, what else can you tell us?"

"I-I don't know!" Nancy stuttered.

"Nancy there has to be something," Sam prompted. "Something we missed, something that-"

"Screw it, there's no time," Dean interrupted, throwing his backpack from around his shoulder. He shuffled inside for a moment before drawing out a can of lighter fluid, and he began to pour it around the room.

"What are you doing!" Nancy gasped.

"Torching the place," Dean said, tossing the empty can to the floor. "There's no other way."

Nancy stumbled out of the room behind Sam, and her eyes widened as the room burst in flames nearly immediately after Dean had thrown the match. For a moment they watched the fire before shielding their faces as the smoke began to engulf them from the frame of the door, and they backed down the hall, only to be greeted by a shrill scream as Charlotte appeared on the other end of the hall, blocking their escape.

"Dammit!" Dean called as he reloaded the gun as quickly as he could, Charlotte meanwhile approaching them slowly, illuminating the hall in a bright red light. Smoke bellowed around, causing Nancy to sink to her knees once more as she struggled for air, her body jumping as the gun fired. This time the bullet hit, causing Charlotte to disappear in flames, and once more Sam was pulling Nancy to her feet and dragging her along as the brothers headed for the stairs.

"Whatever is keeping her here isn't in that room, Dean," Sam sighed once they reached the bottom of the stairs.

"No shit, _Nancy Drew_ ," Dean growled, struggling to determine their next move. Meanwhile, Nancy had once again fallen to the floor, and Dean cursed to himself as he slammed his fist against the wall. Nancy jumped once more, and at the sound of something clanking against the floor boards, Sam and Dean glanced down in unison. Sam's brows furrowed as he bent down to retrieve the object, and the brother's eyes met, locked in an expression of pure frustration.

"What is this?" Sam asked, holding the object to out to Nancy, who wearily glanced up with slitted eyes.

"It was Charlotte's necklace," Nancy breathed, her chest heaving. "An heirloom of the Thornton family. I found it in Clara's room, along with this..." Nancy reached into her pocket to draw out a folded piece of paper, which she handed to Sam, who immediately opened it to begin reading it's contents.

"Well it looks like the fire that killed Charlotte was no accident," Sam reported. "This a receipt for gasoline and matches, signed by Clara."

"You had this on you the whole time!" Dean shouted, looking back to Nancy, who had melted to a pathetic mess at their feet.

"I didn't know it was important."

"Yeah of everything else you found _this_ you deemed unimportant."

"Dean!" Sam called, pointing as Charlotte, who was approaching them fast. "Hurry!"

Dean tossed Sam his lighter before he readied the gun, watching as Charlotte's angry spirit approached, moving faster than ever, but just before she could reach them, a sigh of relief escaped Dean as the spirit went up in a steady burning flame as Sam tossed the burning receipt and necklace to the floor.

It took the ferryman a solid hour to approach the dock, and once more Dean left Sam to assist Nancy into the boat, who continued to mumble to herself about Jessalyn, despite Sam's best efforts to convince Nancy that her friend had perished by Charlotte's vengeance long ago. The ride back to the small town in Georgia took another hour, all the while Sam and Dean remained silent. Once they reached the docks, they left the ferryman to assist Nancy out of the boat, whom after having rested during the ride, appeared to seem a little better.

"Who are you guys anyway?" She asked.

"We're the ones who saved your damn life," Dean said. "And if you're smart, which... you're really just not... you'll stop trying to solve 'mysteries', or whatever it is you do."

Nancy let out a hoarse giggle. "No way!" she said. "Solving mysteries is what I do, and so long as there are secrets in this world, Detective Drew is on the case!"

Shaking his head, Dean held onto his bag as he began for the car, calling after Sam.

"We should team up again!" Nancy called after them. "We make a good team! Goodbye!"

Dean slammed the car door once he was in the driver's seat, and he started the car just as Sam closed his own door.

"Man I swear, if he run into her again... I'll kill her."

Sam smiled. "She's just a naive kid, Dean."

"Yeah but still. She almost got us killed Sammy. She does more harm than good. I mean it, I'll gank that bitch if we see here again. I'll be doing the world the biggest favor."

Sam let out a chuckle. "Yeah well, what the odds of seeing her again anyway?"

Dean paused for a moment. "Yeah, good point," he responded before finally throwing the Impala into gear, the engine roaring as he turned around and began away from the docks. He glanced up to the review mirror, watching the silhouette of Nancy Drew grow smaller and smaller, and for the first time, Dean finally relaxed within his seat.


End file.
